


HiJack Smut Week 2016

by WrC



Category: How to Train Your Dragon (Movies), Rise of the Guardians (2012)
Genre: Ass Teasing, Body Worship, Caught, Come Sharing, Come Shot, Come Swallowing, Coming Inside, Coming inside together, Crossdressing, Crossdressing Kink, Cum Eating, Double Penetration, Exhibitionism, Face-Fucking, French Kissing, Fucking, Hand Jobs, Hiccup in the middle, Incest, Inflatable Buttplug, Kissing, Lingerie, M/M, Massage, Mention of Bondage, Mutual Masturbation, Oral Sex, Orgasm, Overland twins, Public Blow Jobs, Public Hand Jobs, Public Sex, Sexting, Shower Sex, Sibling Incest, Sloppy Seconds, Spitroast, Threesome, Underage Sex, Using toys on each other, Watching Porn Together, dickpics, dragon dildo, mention of stomach bulging, sex in the car
Language: English
Status: Completed
Published: 2016-09-18
Updated: 2016-11-23
Packaged: 2018-08-15 19:47:37
Rating: Explicit
Warnings: No Archive Warnings Apply, Underage
Chapters: 8
Words: 17,742
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/8070361
Author URL: https://archiveofourown.org/users/WrC/pseuds/WrC
Summary: A collection of all 7 days of HiJack Smut Week 2016: 1) trying to stay quiet, 2) Watching porn together, 3) sexting, 4) hickeys, 5) Threesome Thursday, 6) Double Penetration, 7) is this yours?!. Art for day 3 by Syndeh @ tumblr.





	1. Day 1 - Trying To Stay Quiet

**Author's Note:**

> I apologize in advance if these are slightly below my usual level. Due to high time pressure for this week, some days didn't get as much attention as I would have liked. Except for day 3 - that day got aaaallll the love it needed for sure :3. Because that one has pretty art!
> 
> Still, I find all prompts super sexy, and I hope you'll find these lovely little fics as hot as I do. Enjoy~

**Summary for the Chapter:**

> Hiccup and Jack go camping with Stoick and Gobber... tents are thing and sex is loud, so they quickly become rather deprived of physical contact. An issue Jack decides to fix in a shower stall.

 

Hiccup frowned at the shower stall. A small shower-head. A push-button to turn the shower on, probably for a frustratingly short time. An equally small shelf on the wall for one bottle at most, which made Hiccup wonder whether this was the motivation between hair-and-body-in-one stuff. A little division with a hook facing away from the shower, where one might attempt to keep ones clothes dry. Often with mixed success. But at least the floor was clean, which made the stall above average on Hiccup’s ‘shower ranking list’.

He slung his towel over the door, but just as he tried to close it, someone pulled it open again. Before Hiccup could object, Jack had joined him in the small stall. He locked the door and faced Hiccup with a sly grin.

“ What are you doing?” Hiccup whispered, not wanting to draw attention to them.

“I’m joining you in the shower!” At least his boyfriend had the sense to speak equally hushed.

“ I can see that,” Hiccup said, rolling his eyes. “And what do you hope to accomplish?”

“ Aww come on Hic,” Jack whined. “We’ve been on this campsite for a good week now and I haven’t as much as made out with you due to a severe privacy problem.”

“We did kiss. In my tent.”

“Barely. You know what I mean.” Jack made a pouty face. “I wanna love you.”

The problem was that Hiccup was still more or less in the closet. As far as Stoick was concerned, Jack was just Hiccup’s best friend. So two teens, in love, and overflowing with hormones, spend all day together with an absolute minimum of physical contact. Consequently, their sexual frustration had skyrocketed to unknown hights.

The problem with making out in their tent wasn’t with the kissing itself; you can’t kiss loud enough to wake a heavy sleeper like Stoick. But Hiccup knew that if they started making out in earnest, it would not end there. Hiccup always had trouble keeping quiet, and tents were thin. There was no way Gobber’s snores were loud enough to drown out any sounds that might come from the boys’ tent. It was a recipe for embarrassment and a very awkward breakfast at best.

“And you find this cramped stall the right place for that?”

“It’s the most private thing around I’d say. I mean it’s where I jerk off too, so…” Hiccup gave him a look. “ What? Don’t even try to say that you don’t.” Jack grabbed the brunet’s hands and the sly smile returned. Hiccup was too slow to come up with another protest or throw Jack out altogether. The white-haired teen quickly used his indecisiveness against him and kissed him. The moment Jack’s lips touched his, Hiccup knew there would be no further objections.

Hiccup kissed back eagerly, opening his mouth to Jack. Their kiss was hungry, desperate almost, unlike their usual tenderness. Particularly Hiccup, who was the less experienced of the two, was caught a bit off guard. They rarely kissed with this kind of intensity.

Jack held Hiccup close, one hand in Hiccup’s hair and the other on his lower back, slowly rubbing up and down. Hiccup melted into the embrace. He had felt exactly like Jack – endlessly frustrated at not being able to touch his boyfriend, and afraid of what his dad would think. But now they were both shirtless, pressed together in the hot, cramped stall. It was sweaty, and they couldn’t move much or they’d bump into the walls, and Hiccup couldn’t care less. Hiccup’s world had collapsed to just Jack. There was nothing more than the warm arms, the bare torso against his own, the smooth skin under his hands. Their lips pressed together hard, their tongues hungry. God how he’d missed that.

Suddenly, Jack broke away. They were panting slightly.

“Weren’t you going to take a shower?”

“Right,” whispered Hiccup back. He took off his swimming shorts. His dick was already semi-hard. He saw Jack staring at him, and his face started to burn. Jack hated it when Hiccup felt self-conscious, so he quickly took off his own trunks, revealing that he too was already turned on big time. He gave Hiccup another kiss. The teen gasped a little when their dicks touched.

It took a lot of self-control to stop for a moment so Hiccup could take off his leg. He had to hold on to the wall for support because there was nowhere to sit. Jack put his leg somewhere safe from the water. They got under the shower together and Hiccup grabbed onto Jack so he wouldn’t fall over. He directed Jack’s arm under his armpit and around his back. When he was satisfied with the stability of his position, he pushed the button to turn the shower on and went right back to kissing his boyfriend. Again the world was reduced to just the white-haired boy in his arms, now with the added excitement of two boners pressed together between them.

The water washed over them as they made out. Jack reached in between them and slowly stroked both their dicks at the same time. Hiccup moaned softly into the kiss. When he realized what he was doing, he tensed and cut himself off. Jack noticed and gave him a questioning look.

“I almost forgot we need to be quiet”, Hiccup whispered into Jack’s shoulder. The other teen chuckled and squeezed their dicks. Hiccup jerked and breathed hard through his nose. If it weren’t for Jack, he probably would have fallen over.

“Jerk!”, he hissed. Jack gave him a peck on the lips.

“Love you too, honey.”

Determined to get back at him, Hiccup assaulted his boyfriend’s neck with kisses, pecks, and licks. But even when he made a hickey, he got no more than just a slightly louder breath. One look at Jacks face told Hiccup he was doing it right though. How did this guy manage to stay so silent?

Jack could probably guess what Hiccup was thinking and smiled. ‘My turn’, he mouthed. He pulled Hiccup’s foreskin back, exposing the soft pink glans completely to the chilly water. He then proceeded to rub his thumb over the sensitive underside of Hiccup’s glans, making the brunet weak in the knees. Hiccup bit his lip and managed to stay quiet… until Jack rubbed his own uncut dick at the same spot _and_ used his hand to pleasure the rest of Hiccup’s twitching member at the same time. The sound Hiccup produced was something between a keen and a gasp. He clasped a hand over his mouth, eyes wide. God, he hoped no-one had heard that one.

Jack was obviously holding back laughter. Hiccup gave him an angry look. He pretended to get back to Jack’s neck, this time extending his administrations to include licking at his earlobe and nipping at his lips. It was just a distraction, however. The brunet was slowly sneaking his finger towards Jack’s entrance, and he wanted it to be a surprise.

His efforts proved successful. Without his boyfriend taking notice, he’d reached Jack’s asshole. He rubbed his finger over it and pushed gently. He couldn’t actually go in, but the touching was enough. A soft, surprised ‘ah’ escaped Jack’s lips, and now it was the brunet’s turn to look smug.

Jack smiled and playfully wiggled his butt in Hiccup’s hand, rubbing against the finger. This was a battle Hiccup wasn’t going to win, and they both knew it.

The white-haired teen let go of their dicks and slid his hand down to fondle with Hiccup’s balls. That alone was almost enough to entice a sound from the brunet again. He pulled Hiccup closer and moved his hips, rubbing their hard dicks alongside each other. Hiccup was in heaven. Jack’s wet stomach on the underside, Jack’s hardon pressed against his own… Sadly the plan partially backfired, for the white-haired teen himself had some trouble staying quiet at this. That, and Hiccup bit down on his shoulder to keep himself from moaning; something he’d never done before and Jack somehow found damn hot.

Hiccup gently pushed against this boyfriend and he stopped. He motioned to his leg; he was getting tired. The fact that he also was about to cum, he didn’t share. He made the gesture of blowing Jack, who was absolutely delighted. He couldn’t imagine ever turning down a blowjob from this lovely boy.

Hiccup got down on his knees in front of Jack. He wasn’t really under the shower anymore, but that was okay. He grabbed onto Jack’s hips and kneaded his ass. In truth Hiccup was just as impatient as Jack to start sucking, but he wanted to get back at him first. So he dragged his tongue all over Jack’s balls. It had been a while since Jack had shaved, but Hiccup didn’t care. Hell, they already did this before either of them started shaving at all.

When the brunet sucked a testicle into his mouth, a sharp intake of breath was heard over the clattering water. He let it plop out and lapped at Jack’s sack. He worked his tongue and buried his mouth in Jack’s crotch till his short brown pubes tickled at his nose.

Jack couldn’t suppress a whine. Hiccup looked up with innocent eyes but failed to keep a mischievous little smile from his face. ‘I’m close’, Jack mouthed. That wasn’t very surprising. Although Jack usually lasted longer on account of being cut, Hiccup himself had been at the edge just moments ago.

Finally, he took Jack’s hard dick in his mouth. He moved his tongue over the slit and along the downside of Jack’s dick. Hiccup moaned softy as he went deeper, yet the white-haired teen remained silent. Hiccup wanted to coax some more noise from this boy, no matter what. It had become a matter of pride to break his self-control.

Determined, the brunet went back up, sucking hard. He licked at Jack’s most sensitive parts and went back down, taking Jack as deep as he could without gagging. He used his hand to jerk off the part that didn’t fit in his mouth. One more bob up and down is all Hiccup got before Jack came.

When Hiccup felt the first shot of cum, he let Jack plop free of his mouth. He continued to jerk him off, letting the cum drip down on the shower floor. Finally, at long last, Jack made some clearly audible noise.

It was still a held-back groan, but it was a groan nonetheless.

When Jack was finished, Hiccup sucked up and down his dick a few more times, ignoring the in his opinion unpleasant aftertaste of sperm. Jack tapped his shoulder and he stood up again, this time he used the wall for support.

“That was awesome”, Jack whispered. He gave Hiccup a quick kiss. “I’ll return the favour. Try not to alert the entire shower-block, all right?”

They switched position. Jack double-checked that his boyfriend was stable enough, concerned that he might fall over. The brunet gave him an encouraging nod.

Unlike Hiccup, Jack had no intention to tease. He wasted no time and went down on Hiccup’s rock-hard cock, taking almost the entire length. Briefly, he felt brown, curly hairs tickle at the tip of his nose. When he came back up, he saw Hiccup with his eyes closed, biting on his fist. Jack smiled and pulled back Hiccup’s foreskin, lapping around the sensitive head. As expected, there was an abundance of slightly salty precum. This wouldn’t take long at all.

Hiccup’s soft pants, gasps, and moans were only just covered up by the noise of the steady stream of water. Keeping the head exposed for maximum pleasure, Jack rapidly sucked up and down. A few more strokes and a fleeting touch of Hiccup’s ass was all it took to set him off. Jack swallowed everything. He kept licking and suckling till the last drop and Hiccup started to go soft again. By then, the water had long stopped. They’d forgotten to press the button again.

When the brunet came back down to earth, they noticed the water in the neighboring stall had stopped as well. The sound of someone jerking off was unmistakable. The boys shared a look and blushed. If they could hear their neighbour so well when the water was off… he must have been able to hear them just as clearly. Where they the cause of his arousal? It turned Jack on all over again.

It was rather evident when their neighbor was done as well, and the water was turned back on. Both teens finished their own shower (Hiccup still needed to wash his hair after all) and dried off. The lack of mobility on Hiccup’s end made it all take a bit longer than it could have, but Jack was patient, acting as human crutch when needed.

When they finally exit the stall, they expected their partner in crime to be long gone. Hiccup looked around and confirmed they were indeed alone. No other stalls were occupied, thank God.

But then he noticed a black-haired guy at the exit of the shower complex. The teen sees him looking, turns bright red, and runs off.

Jack laughs. “I swear I saw him mouth ‘holy shit’ before he ran off.”

 

 


	2. Day 2 - Watching Porn Together

**Summary for the Chapter:**

> Jack finds out he isn't the only one that watched porn despite their abundance of sex. So why not watch together?

  
“Hey Hic?”

“Hmm-hm?”

“We have sex pretty often, right?”

The brunet looked at his boyfriend, arching an eyebrow.

“Ehm… yes, I’d say so? If this is a suggestion to do it right now, I must say you could have worded it a lot better.”

“No no no, that’s not the point. I just seriously wonder: do you still jerk off as well?”

Wait, what? Hiccup swallowed and nervously averted his eyes. In and of it’s own, the fact that he did still jerk off wasn’t that weird - he believed most people masturbated, relationship or no. He was a bit embarrassed to admit how often he did it though, in addition to their abundance of sex.

“Yes…”

Jack sighed.

“Thank God I’m not the only one. I thought I was weird for doing it even though we make love like…” Jack thought for a moment. When he completed the math in his head, his eyes went wide. “Holy shit we do it at least four times a week.”

“No you can’t be right… wait, yes, you are. Damn.” Hiccup gave Jack a worried look. “Is that weird? Or worse, does it bore you? Because you totally shouldn’t say yes just because I-”

“Don’t spew such nonsense”, Jack cut him off. “Boring and sex are two things that have absolutely nothing in common as far as I’m concerned. I love you and I love doing it with you.”

“Do you think it’s a lot?”

Jack shrugged. “I don’t care, honestly.”

“I suppose you’re right.” Hiccup nodded and sat closer to Jack, leaning into his boyfriend comfortably. They watched TV for a while before Jack broached the topic again.

“How often do you do it though?”

The brunet blushed and hid his face against Jack’s arm, mumbling something the other didn’t quite get.

“Come on Hic, don’t be embarrassed”, Jack said, laughing. “Tell me!”

Hiccup mumbled again.

“Fine I’ll tell you first then. I usually do it if I’m home alone during the evening, or when you’re staying the night somewhere without me. Besides that I’d say once a week.”

Hiccup disengaged his face from Jack’s sleeve. “Do you use anything?”

“Just porn and my hand. Now out with it, you nerd. What about you?”

Again, green eyes couldn’t maintain contact with their blue counterparts. Hearing Jack did it too didn’t really help much with Hiccup’s embarrassment, which was mostly focused on the frequency of his masturbation endeavors.

“I cum like… once a day. Sometimes it even happens that I jerked off during my morning shower and we end up having sex in the evening.”

“Oh wow. Can you, like… cum more than once in a row?”

Hiccup’s cheeks turned an ever darker shade of red.

“It’s been a long time since I did that… but yes I used to.”

“Awesome, we’re totally gonna try that some time soon. ”

“I was even worse back in college. When I had to study for exams, I could easily do it twice or thrice a day.”

“Same though. I’m just really surprised that you do it even more often than me. Do you use anything to aid the process?”

Hiccup shrugged. “When I’m absolutely alone I use toys. Otherwise just porn.”

“Of course. The internet is for porn. The internet is for porn!” They both giggle as Jack proceeds to sing the song. “So grab your dick and double click for porn, porn, poooooorn!”

“Jack, shut up, the neighbours will hear.”

“They’ve heard worse.”

“And whose fault is that, huh?”

“Hey now, let’s not focus on blaming anyone for anything. Let’s discuss porn instead.”

“Classy.”

“You know me. What do you like to watch?”

“Really, we’re having this conversation?”

“Not if you don’t want to, buttercup.” Jack held up his hands. “I just wonder if we look at the same things. Who knows, maybe it’ll reveal a new kink here and there.”

“Our sex is not kinky enough?”

“That’s not what I said.” Now it was Jack’s turn to blush a little. It was only yesterday that Hiccup had worn an incredibly sexy, lace thong just for Jack. He had fucked the brunet while he wore it, and it was one of the hottest things he’d ever done. It was clear his boyfriend was trying to steer clear of the topic at hand though, so Jack let it slide. Sort of.

“Let’s try something else then. Let’s watch porn together.”

“What? Why?”

“Because I think it will be totally hot. And we’ll probably end up having sex anyway, porn or no porn, right?”

Hiccup laughed. He had to admit that was probably true. There was no way he was going to keep his hands to himself for the rest of the night after this rather liberating conversation. Maybe even try the double cum thing, since he hadn’t done anything yet today.

“OK, why not. Bedroom?”

“Puh-lease! When we have a smart-TV in the living room? I wanna enjoy whatever you pick in it’s full HD glory.”

“Sorry to disappoint you, Jack, but amateur isn’t usually in HD.”

The white-haired man was already closing the curtains, however. He snatched the keyboard that was synced to the TV from the coffee table and sat back down with a satisfied sigh. Hiccup didn’t fail to notice that his boyfriend adjusted his already growing dick in his pants while he offered the keyboard. The brunet declined, insisting the other went first. Jack then proceeded to put up some fairly standard Helix studio porn. It was pretty generic gay stuff, but Hiccup didn’t mind much. Helix had some of the hottest pro’s in the industry.

It wasn’t a full movie, and ten minutes later it was Hiccup’s turn. He was sporting just a semi-hardon, although he could clearly see Jack was at full mast.

His porn of choice was just as decent as the previous video. Same studio, different actor, sweeter voice than before. Hiccup turned the sound down a bit, just to be sure the neighbours couldn’t hear them. Again, it was a short video (who even has the subscriptions to watch full length material anyway), and the keyboard went back to Jack before there was any satisfying closure.

Tired of the generic shit that he didn’t even like all that much, Jack found some amateur emo videos. It was one of his favourite genres. While a black-haired boy was getting fucked against the wall, Jack slid his hand in his jeans, palming his dick. Hiccup noticed. His boner immediately grew to full size. The porn might not be the hottest in the world for him, seeing Jack like this was.

By the time the video was over, Jack had his pants on his knees and his dick out. Hiccup had ditched his jeans, but his boxer briefs were still in place, showing the clear outline of his cock in the red fabric. He idly rubbed over it while he looked at Jack’s hard, sexy dick. It was his turn to pick something, but he didn’t know what to show Jack.

“You’re more getting off from me than the porn. Pick something you really like.”

“Well…” Hiccup looked away.

“Hiccup, honey, look at me.” Green eyes met bright blue ones with more than a little reluctance. “We’ve been together for an incredibly long time - which I still greatly enjoy by the way - and we have seen, touched, and tasted every inch of each other’s body’s, plus some bodily fluids. There is absolutely nothing you should be ashamed about. Not with me.” He let the words sink in for a second. “I proposed this because I think it’d be hot to see what gets you off when you’re alone. I am curious. But I won’t judge. And if you rather just have sex at the moment I swear to God I’ll take you right here right now. Your call.”

“Well… you see… I don’t think you’d like it.”

“Tell me what it is first then.”

“Ehm… one thing I like to see is ehm… extra large dildo’s? Like, dragon dildo’s and the like? With stomach bulge is even better.”

Jack’s eyes went wide. That’s what Hiccup looked at? Oh boy, this was going to be quite something.

“Do you… do you just like to see it or, you know…”

“What?”

“Do you want to do that yourself too?”

“Oh God no. That’d hurt like hell. No offense, but I love the fact you’re average, Jack.”

Jack laughed. “Well, what are you waiting for then? Put it on!”

“Seriously?”

“Yeah, I don’t mind. It’s your thing and if it’s not my turn-on I’ll just watch you instead.” With a sly smile, he added: “You never fail to turn me on.”

Hiccup kept his eyes to the TV and found a suitable video with great ease. He must have looked at this one a lot.

The video was pretty much what Jack expected. A hot, slim guy and a long green/pink dildo. It was rather thick at the tip and impossibly big at the base. And to Jack’s amazement, most of it went _in_.

What was more interesting though, was Hiccup’s reaction to it. The brunet had his dick out. He was stroking himself with long, slow strokes, enveloping the head with his fist and going all the way down to the base, baring the glans on every stroke.

Jack had to admit the twink on TV produced the loveliest moans when his stomach bulged. Yet Hiccup’s little gasp was sweeter still. He squeezed his dick harder and Jack reached over to cup his balls. At first his boyfriend started, but he quickly relaxed, opening his legs wider.

“I never thought this would excite you so much,” Jack said when the video was over. “I’m so curious to see what you’ll put up next. But first…” he looked up a short clip of his own choosing. “This beauty.”

While a cute, crossdressing twink was drilled into the mattress, the two young men decided to lend each other a hand while watching. Jack moaned blissfully when his lover started to rub his thigh and fondle his balls with his free hand. He could totally get lost in this treatment. The video was over, of course, before he could.

“Okay, your turn again.”

“How would you feel about some hard spanking?”

“I thought you didn’t like that?”

“Not if I’m being spanked, and I’m too much a softy to spank someone myself. But vids are… I don’t know. Hot.”

“I won’t question it,” Jack laughed. “But maybe something a bit milder so I don’t lose my boner.”

Being considerate, the brunet went for something with a jock-strap wearing bottom that produced lewd sounds while a very long dick was fucked into him. Jack found it acceptable too, and busied himself with looking at his boyfriend, occasionally touching his soft sack or licking a nipple. How Jack savoured those soft sounds his lover produced.

When it was done, Jack’s counterpick involved voyeurism, and again Hiccup gave him a helping hand.

“Oh shiiiit,” Jack sighed. “Keep going Hiccup. I’m gonna…” Hiccup squeezed harder and went just a bit faster, barely tracing his fingers over Jack’s balls at the same time. “I- I’m gonna- OH Hiccup! Aaaaahmnnnnn!”

Hiccup felt the smooth sack contract under his soft administrations. Jack’s dick started to pump. Thick, white sperm flowed down over his hand, making it slick and sticky, and a little pool formed on Jack’s stomach.

“Hmmmnn fuuuuuck,” Jack gasped.

When Jack’s moans returned to mere sighs and his cock stopped oozing, Hiccup bent down. He gave the tip a quick suck, cleaning it off and licking up the last bits of cum. Jack yelped. He was so much more sensitive than Hiccup after coming - a fact the brunet liked to abuse from time to time.

“Damn. That was awesome. Shall I suck you off while you look at something? Doesn’t matter what, I’ll be too busy to see it anyway.” Jack said with a wink.

Jack didn’t see his boyfriend’s choice, but it sounded pretty hard-core. Again probably something Hiccup would never want to do himself, but somehow found incredibly hot to watch. Jack just focused on the rock-hard member in his mouth.

Hiccup came, shooting releasing a load of sperm into Jack’s mouth. His boyfriend didn’t stop though; not even when all the seed was long gone.

“Fuck Ja-HAaack!” Hiccup groaned and writhed underneath him. “I just came! AaahhHAAH!”

The mischievous little shit ignored any complaints. Hiccup said he could come twice, and Jack was dead-set on finding out how big that second load was going to be.


	3. Day 3 - Sexting

**Summary for the Chapter:**

> What do you do when you're apart, missing each other, and kinda horny? Exactly. Dickpics.

**Notes for the Chapter:**

> Amazing art by Syndeh (syndeh.tumblr.com). Seriously, go to his tumblr and give him some love!  
> It was awesome to collab with you, Syndeh!

  
J: Hiccup I miss youuuuuuu

Hiccup chuckled at his phone. Not a day went by without Jack telling him how much he missed him. If international calls weren’t so ridiculously expensive, Jack would surely call him at least once a day too.

H: I love you too snowflake <3

It wasn’t easy being separated by the entire Atlantic ocean. Hiccup had followed his ambitions and went to Cambridge University, while Jack stayed closer to home and got into Berkeley. So now they didn’t only have the chaos of their first year at college and all the stress that brought with it, but also the added pain of being very, very far apart.

Regularly skyping and texting each other was the only thing that made it bearable for Hiccup. He couldn’t share his every moment with Jack like he used to, but at least they could give each other recaps of their day once every 24 hours. So Jack could still hear about the freshman that poured monster energy in his coffee during the early morning lecture, and Hiccup still heard what silly hat the lady in Jack’s street was wearing that day.

J: She was wearing a pink one with flowers today, by the way.

H: Let me guess… Green jacket underneath so it clashes nicely with the hat?

J: You got it. And the flower was orange.

H: Wow. She really must be colourblind, there is no other explanation.

J: Or maybe just blind?

H: *sigh* I miss this. I can’t wait for our skypecall this weekend.

They usually agreed to skype during weekends, when Hiccup could stay up as late as necessary and Jack could come online early. That way, they had a few hours they could spend together. The brunet has also fallen asleep while skyping and watching a movie together on several occasions. One time, he was still within view of the webcam. Jack had stared at his peaceful, sleeping face for a while, listening to his soft snores.

J: I think I miss your freckled face most.

J: Or maybe your nose.

J: Or maybe your hair. I have nothing to braid now.

H: Are you going to list my entire body now? XD

J: Most of it anyway. Can’t say I miss your left foot.

H: Don’t you dare

J: Only you miss your left foot

H: ….. -.-;

J: I miss your lips too though. Your touch.

J: Your back with the endless constellations of freckles.

J: Your soft hands.

H: Jack, you’re making me blush >///<

J: Your smooth stomach. Your treasure trail.

H: Jack…

J: And don’t get me started on that ass.

H: I so miss your hands on my ass at the most inappropriate moments.

J: Boy would I like to fly over just for that booty

H: I can’t wait for holiday, I want to hold you again.

J: And fuck each other’s brains out?

H: So romantic

J: You know I’m right :P

He was right. Hiccup was sure that when he came home, Jack would be at the top of his priority list. They would spend the night together as soon as he was back, jetlag or not. Probably with pizza and netflix. And then they wouldn’t last through the opening credits without jumping on top of each other.

Not that their entire relationship was based on sex, of course. But the lack of it wasn’t pleasant either.

H: How are we going to survive this level of sexual frustration till we see each other again O.o

H: We’re doomed!

J: Oh thank god I’m not the only thirsty fucker here

H: I would reply with a list of things I miss about you… but then I’d get unbearably horny.

J: Too late for me.

H: Gdi Jack why do you do this to me xD

J: I miss your dick too.

H: So classy, Jack.

H: I think we’d need an entire week to catch up with all the thoughts I’m having right now

J: Tell me the best one

H: You tie me up and fuck me?

That was something they’d only done once, not long before Hiccup moved away.

J: Shiiiiiit

J: That was so hot

J: Do you… wanna exchange pics?

H: You mean like phonesex?

J: Well we’re pretty much doing that already. Might as well make it visual.

H: I don’t know…

H: I don’t like the idea of my nudes floating around on KIK

J: How about snapchat. Just install it and I’ll add you.

J: It’ll be hot as hell, trust me

Hiccup gulped. He’d done a lot with Jack, but he’d never exchanged pictures with him. There was no need, since they saw each other so much, and it wasn’t a particular fetish of either of them. But now… Hiccup was hard all right, and seeing some of Jack’s hot body would definitely help him with that. He assumed Jack felt exactly the same way.

He set up the account. With his heart pounding in his chest, he gave Jack his username. Soon enough he was looking at Jack’s happy face. His boyfriend was still in bed, and from the looks of it had a terrible case of bed-hair. Hiccup sent a smiling selfie back.

J: OK, I’ll start with something more sexy ;)

Hiccup got the picture. The covers were pushed down to just above Jack’s crotch, showing of his entire torso and stomach. Hiccup gulped and replied with a similar picture. He was still wearing his pants, but you could clearly see the outline of his hard dick.

J: Damn that’s hot.

H: Back at ya. Show me more, I’m too damn hard now

Jack sent another snap and Hiccup’s heart skipped a beat. The covers were entirely gone, Jack’s thick dick held upright in his hand. He was still smooth all over, save for the little line of hair they both liked so much. The foreskin was pulled back to show off the soft, pink glans.

Hiccup quickly undid his pants and released his dick. He was hard as a rock. Already, a drop of precum leaked out. He didn’t really know what to do with his expression, so he just sort-of smiled.

 

  


It was awfully quiet after that. The brunet had expected an instantaneous reaction from Jack. Had he done something wrong? Did something happen?

J: Holy fucking fuck that’s hot

J: Sorry, late response. I had to recover from that picture

Not long after, Hiccup got a short video where Jack slowly jerked his dick. The white-haired man moved his hand up and down in a long, deliberate motion, the head briefly disappearing in his fist. Hiccup replied with a closeup of his boner taken from below, so his face was visible as well. His boyfriend sent another video, this time showing both his face and his foreskin sliding over the moist glans. It had the caption ‘Shiiit so hot’. Jack’s expression was a huge turn-on for Hiccup, who tried to reply with a video of his own - with moderate success. Filming at a decent angle and feeling good at the same time turned out to be more difficult than he’d expected. He decided it would be better if he stuck with pictures for now.

The brunet was more successful at shooting a picture of his ass, taken upon Jack’s request. The other responded in kind, of course. Hiccup jerked off hard while he stared at his boyfriend’s smooth, smoking hot ass. He groaned in frustration when the picture disappeared again and he was forced to ask for another.

 

  


‘Use a toy’, Jack’s latest snap read. That was a bit of a surprise, but Hiccup decided that a vibrator definitely fit his current mood. He rummaged around in the box under his bed and produced a black, silicone vibrator. Hiccup never told Jack, but he’d bought this particular one because it was the closest he could find to Jack’s dick-size and shape.

He lubed it up and fingered his hole in preparation. Lube on your hands and snapping are a tricky combination at best, so the white-haired teen filled the silence with pictures. They all looked quite alike - Jack stroking or showing off his cock with the foreskin peeled back - but Hiccup didn’t mind. It was hot as hell and he couldn’t get enough of it. Sometimes Jack would send one with a better view of his smooth-shaved balls, or a closeup of the tip, and Hiccup would moan and speed up till he was about to cum. Then he’d stop and cool down until he got the next picture, because no way in hell was he cumming already.

At last, Hiccup pushed the vibrator inside. He closed his eyes and imagined it was Jack that gently moved into him. Slowly, he slid it in and out for a while, getting used to the size. Jack - and thus this vibrator - was on the thick side, so he needed to take his time.

Then he turned it on. Intense pleasure waved through him. He moaned loudly, arching his back, and pushed the vibrator as deep as it would go.

He wiped one hand clean and made a few pictures for Jack, showing off his handiwork.

J: Jesus

J: Fuck

J: You’re so sexy

The exchange continued, and Hiccup showed off every bit of himself to Jack. His precum leaking dick. His balls, drawn close to his body in arousal. His ass with half of the vibrator sticking out. A short video where he managed to show the vibrator going in and out of him. His wanton moans. All was sent to Jack.

H: I wish it were you fucking me

J: When you get home, I’m fucking you all night in every position imaginable

Hiccup blushed. Even now, after all this, Jack could still make him blush. Frankly it was ridiculous.

H: Doggy?

It was his favourite position. Jack had fucked him like that with his hands tied behind his back the night before he left. He’d been in pure ecstasy.

J: You bet your sassy ass. And Jerk you off while I do it.

H: I’d come way too quickly…

J: Then we just recover and go for round two. All. Fucking. Night.

J: I swear.

H: And in the morning we’ll do it all again, only in reverse

J: You know we would. I’d wake you up with a blowjob

H: Ride me

J: Fuck me good

Lying on his back, the brunet thrust up into his fist, pretending it was Jack. He filmed it.

J: God yes like that

J: You’d make me cum all over you

Eventually, they ran out of requests and poses to send each other. That didn’t stop them though. They just repeated the ones they fond hottest, accompanying their snaps with things like ‘more dick’ or ‘ass pls’, and the occasional ‘fuck that’s so hot’. They both agreed that pics with face were the biggest turn-on - Hiccup just loved seeing Jack’s expression when he’s on the edge of coming.

J: I’m close. One more with all of you.

Hiccup obliged, trying hard not to look like a total idiot because of the vibrator that was still up his ass, giving him continuous pleasure.

 

  


J: Check KIK

Hiccup opened the app just as he received a video from Jack. It was captioned ‘so you can look at it more than once’. Apparently Jack didn’t share Hiccup’s reservations towards using KIK for nudes. The brunet didn’t mind in the slightest. The video was one of the hottest things he’d ever seen.

Jack had gone through the trouble of setting up his phone to film. He was jerking off rapidly. His hand was a blur and his foreskin made slick noises. Hiccup’s name and ‘oh fucks’ spilled from his lips, alternated with the occasional moan or gasp. And then, he came. His perm shot out, splattering on his stomach. The blue hoodie was only just held back far enough to avoid the cum.

 

  


Hiccup groaned. He wanted to show Jack how hot this was, but he didn’t want to stop watching the video and switch back to snap. Hell, he didn’t even want to touch his phone, for that meant letting go of either the vibrator or his leaking dick.

J: How hot was that? ;)

Shit. Jack knew full well how hot that was. Hiccup kept pumping, but he knew his orgasm was fast approaching. He wanted to cum so bad. But first… he had to return the favour for Jack.

Filming with one hand, he fucked himself hard with the vibrator. Hiccup let himself go, not giving a rats ass about what the neighbours might hear. The apartment was filled with the sticky noises of his vibrator sliding in and out, accompanied by loud moans and groans. The brunet told his lover how he wished it was him pounding his ass instead, and how close he was to cumming. Panting, he let go of the vibrator. He double checked his face wasn’t showing and sent the video.

He put his phone down again. The moment he touched his dick, he came. His dick exploded, sending sperm all over his chest and stomach. He gave a low, satisfied groan as he continued to milk his cock, squeezing out every last drop. His hand slowly moved up and down as one of his greatest orgasms ever faded away. The vibrator slipped from his ass and buzzed against his thigh, but he couldn’t be assed to move.

Back on snap, he got another picture of Jack eating his own cum saying ‘thank you’.

Still basking in the afterglow of his intense orgasm, he sent a picture of his own mighty mess.

J: Shame I’m not there to clean it up.

Hiccup wiped a finger through is cum and tasted it. He made a face. Still awful. How Jack could actually like it remained a mystery to him. But it made his boyfriends very eager to give blowjobs, so he didn’t complain.

H: I wouldn’t have had this mess to begin with if you were here.

J: Then where would you have cum?

H: Probably your mouth. Maybe your ass?

J: :P

H: I’m gonna go and clean up, brb

J: Same

A while later, the white-haired teen came back online.

J: We should totally do this on Skype sometime, this was soooo hot

J: Hiccup?

J: Did you fall asleep or something?

Hiccup, however, did not respond. It might have been early for Jack, but it was past midnight in Cambridge. So Hiccup had indeed fallen asleep, clad in only a clean pair of boxers. His phone vibrated a few more times, but Hiccup kept snoring softly.


	4. Day 4 - Hickeys

**Notes for the Chapter:**

> This is my 'break'-day this week, with just a short little drabble~ Also, Jock/Nerd because why not.

“Jack, for God’s sake I’m wearing this turtle-neck for a reason.”

Hiccup fake-punched the jock in the shoulder. The boyfriend in question then proceeded to give him ‘puppy-eyes’.

“But Hiccy, hickeys look so good on you~”

“Oh no you didn’t.”

Jack grinned. “Oh yes I did.”

“Just stop putting them in my neck!”

“But you get all weak in the knees when I kiss your neck, it’s fun. And don’t tell me you don’t like it.”

“I do,” Hiccup was forced to admit, “but I don’t want friggin hickeys there! No matter how much it would fit with my name. Anywhere but there!”

“Okay, I'll put them somewhere else.” Jack tried to lift his shirt.

“Oh come on!”

Jack just laughed and hugged Hiccup instead.

“You cute little nerd.”

“Doofus. Besides…” now it was the brunet’s turn to sport a mischievous little smile. “I know your weakness too.” He gently pushed his hand against Jack’s crotch. Immediately, something started to stir.

“Point taken, point taken! This is hardly the place for that!”

“Glad you feel the same way.” Hiccup adjusted his clothes again. “Break is almost over… will we hang out today?”

Jack nodded. “I’ll drop by after practice.”

“Great, see you then.”

Hiccup, being the shorter one, got up on his tiptoes to kiss Jack, who found that way too and funny waited just a bit longer than necessary before bending down.

“And be sure to shower well. I don’t like sweaty dick.”

“Love you too, you little sex-devil.”


	5. Day 5 - Threesome Thursday

**Summary for the Chapter:**

> Hiccup is on a epic road-trip with the Overland twins. Adorable things and sexy sin ensue.

**Notes for the Chapter:**

> Incest is Wincest, amiright??
> 
> Also, so sorry if there are weird or rushed things in here (or, God's forbid, typos). I was short on time for this one >.

 

The landscape swooshed by outside the car window. Hiccup stared out over the empty countryside, humming a long with _Carry On Wayward Son_ on the radio. They cruised down Highway 2 with still plenty of miles ahead of them before their next overnight stop at a motel. Their ‘epic road trip of awesome’, as Jack referred to this endeavour, had only just begun, but already Hiccup knew he’d made the right choice when he came along with the Overland twins. Sure, they could be quite the characters, but that was part of their charm.

“Hey Hiccup?” Jack was sitting behind the passenger seat. He reached forward to sort-of hug his sort-of boyfriend. Sort-of, because hugging someone from the backseat was difficult, and neither was exactly sure about their relationship status. They just kinda were, and Jack nor Hiccup dared ask what exactly.

“Yeah?”

“I ehm… I… do you ehm…”

That was unusual. “You sound tense, Jack. Something wrong?”

“Oh come on just tell him already, you wuss,” Jackson said. “If you don’t I will!”

“I know I’ve never said it but… well…”

Hiccup was getting thoroughly confused now.

The white-haired teen took a deep breath and his eyes looked everywhere but Hiccup, even when the brunet tried to turn around a bit in his seat. He looked like he was struggling to find the right words, something that didn’t happen to Jack often. Finally, he blurted out: “Do you wanna fool around in the backseat?”

Jackson laughed so hard Hiccup was afraid they might drive off the road and crash.

“What that idiot meant to say was a simple ‘I love you’, but that’ll work too I guess.”

“Oh shut up you jerk,” Jack called at his brother.

He kept laughing, wiping a tear from his eye. “Nothings says ‘I love you’ like a roadtrip blowjob I suppose.”

The poor green-eyed passenger still didn’t quite catch up. Jack loved him so they weren’t sort-of boyfriends? Or was this some joke? Did he really want to get in on while driving? Had everyone gone batshit?

Jackson saw the look on his face and took pity on him.

“Look, Jack is too much of a pussy to come out of the friends-with-benefits-limbo you guys are in, even though it’s pretty obvious that he can. I had to help him a little.

“This is your way of helping?” Hiccup asked.

“He would have done the same for me. Now get into that back seat.”

“Whoa whoa whoa hang on a second.” Hiccup held up his hands. “Is this some team-tagged prank or am I going insane or what?”

“It’s not a prank, Hiccup,” Jack said behind him. He withdrew his hand and the brunet turned around. The white-haired teen looked honestly distressed and a bit hurt.

“I… I’m sorry, Jack. I’m so glad I can finally call you my boyfriend in earnest instead of ‘it’s complicated’. That’s so much better!” He smiled warmly at his now no longer sort-of-boyfriend but actual full-on lover.

“Oh you guys I’m gonna need a bucket. This is too sweet for me,” Jackson interrupted. Hiccup ignored him.

“But really,” the green-eyed teen went on. “Fool around on the backseat?” He arched an eyebrow, but Jack didn’t even look a little bit ashamed.

“What, I panicked okay?”

“We’re in a car with your brother, for crying out loud. It would be downright unethical to make out and force him to listen to that while driving. Not to mention awkward as hell for me.”

“Who said I only wanted to make out?” Jack said with a smile Hiccup knew all too well.

“Although he’s probably equally hot as you on account of you being identical twins-

“Aww thanks, Hic”

“-I have never seen anything more of him than this.” He motioned to the fully-clothed brother behind the wheel. “Going that far while he’s here would be wayyyy too uncomfortable.”

Jackson shrugged. “We have to do something to stay entertained while driving.” He laughed. “I’ll get my fun while you’re driving.”

Hiccup already knew the twins had fooled around on many an occasion - they’d taught Hiccup how to kiss together - so he wasn’t surprised by that. But that they’d want to do it with him there was kinda uncomfortable and hot beyond measure at the same time.

“Also,” the white-haired teen started. “That’s not entirely true Hiccup…”

“What?”

“You have seen more of Jackson than you might think. Or rather you have felt more of Jackson, since it was probably dark.”

“What the hell are you talking about?”

Jackson laughed. “Are you gonna tell him or should I?”

“We traded places once when we were about to get started,” Jack admitted.

“I fucked you and sucked you off,” his brother added.

Completely baffled, Hiccup stared out the window, trying to recount all the times he’d had sex with Jack and figure out which time had been Jackson. They hadn’t done it often in such darkness that Hiccup wouldn’t have been able to tell Jackson’s brown hair from his brother’s white, so there weren’t many options. Still, his mind came up blank.

“Last winter, before Christmas,” Jackson helpfully supplied.

“Holy shit.” Hiccup remembered. Jack had been… different then. “That explained your more than normal enthusiasm… a bit too rough on my ass, in fact.”

“Sorry about that,” Jackson said sheepishly.

“But damn that was one of the most eager blowjobs I’ve ever gotten. So that was actually you… I’ll be damned.”

“Glad you’re not mad,” Jack tried.

“Ha in your dreams, asswhipes. That was a total dick move for not telling me. All the while I was thinking Jackson wasn’t into me like you, Jack. If I’d know that he was, we would have had so many threesomes by now.”

“Well guess what? We’re on a roadtrip now, the possibilities are endless!”

The brunet laughed. “Yeah, but you guys owe me. You’re gonna make it up to me!”

“All right,” Jack started.

“What is it that you require,” Jackson said.

“I don’t know yet, but I’m sure I can come up with some things the next few days!”

Hiccup was once again sort-of hugged from behind. “Whatever you want, buttercup.”

“Oh no you don’t.”

“Cupcake?”

“Just because we’re boyfriends for real now doesn’t mean you get to call me stupid names.”

“Cup-cup?” Jackson butted in.

“Not you too!”

“Hic-Hic then?”

The brunet screamed in frustration.

“Hiccy?” Jack continued.

The brunet sighed. “Acceptable. But no further than that.”

“I promise. Cross my heart and hope to die.”

Hiccup put his head against the window. “This is going to be a looooong trip.”

Once the twins’ laughter had died out, there were only the lyrics of _Free Bird_ filling the car. Ronnie Van Zant sang how he couldn’t change and the song rolled into a guitar solo.

“Are you coming to the backseat or what?”

 

*

 

Jackson briefly stopped at the next opportunity so Hiccup could join the other twin on the backseat.

“Why are we doing this again in a car? With your brother there?”

“I owe you. You said so yourself. I want to start making it up to you, so…” He kissed the brunet’s neck. “…if you’ll allow me…” He rubbed his hand over Hiccup’s crotch, palming the rapidly growing dick. “… I’ll make you feel real good.”

Hiccup moaned softly. “How can I say no to you like that?”

“And don’t mind me!”Jackson said. He adjusted the rear-view mirror so he could see the boys properly. “I’ll just sit here with a tent in my pants and try not to crash.”

“There are worse ways to die than while getting sucked off,” Hiccup mumbled. Jack laughed and continued to kiss his boyfriend. With deft fingers he freed the long, uncut cock. The brunet lay back and closed his eyes, letting Jack do his thing.

With one hand, Jack cupped the smoothly shaved balls, keeping pants out of the way at the same time. With his other, he slowly stroked Hiccup’s cock. He stared at the foreskin sliding up and down, endlessly mesmerized.

“Bless your parents for not cutting you,” Jack said. “I love this so much.”

He dipped down, licking and suckling at the tip. Hiccup sighed and put a hand in Jack’s hair. His boyfriend knew very well how to please him, and he wasted no time driving him crazy with fingers and tongue alike. The brunet tried to stay quiet and not moan too loudly on account of Jackson still being there. It was a bit embarrassing to get all vocal now.

When Jack swirled his tongue around the head a few times, Hiccup couldn’t help it and moaned anyway. He blushed, because he knew the best was yet to come. He pushed a bit on Jack’s head, who quickly got the message. The white-haired man took a breath, relaxed as best he could, and went all the way down. Hiccup’s balls touched his face, and he held there, swallowing hard and suppressing the urge to gag.

“Oooooh fuuuuck yes,” Hiccup groaned. Warm. Wet. Soft. Moving. Oh god he could feel Jack’s throat moving around him. When he came back up, there were sticky strings of saliva running from the tip to his mouth. He briefly caught his breath and went right back down. Hiccup gasped and bucked with his hips, even though he couldn't possibly go any deeper.

Even Jackson was uttering soft curses from the driver’s seat.

“I knew he could suck dick, but I didn’t know he could take _that_!”

Neither of the boys on the backseat could reply. Jack had his mouth full and Hiccup was too lost in pleasure to be able to form any kind of words. He gently, lovingly stroked Jack’s white hair while the teen went to town on his cock. Up and down he went; sometimes all the way, sometimes staying at the tip and jerking off the rest.

Jack swallowed everything when Hiccup came. He gave Hic’s dick one more long, sensual suck up and down and let it plop out of his mouth.

“Shit, that was awesome.”

“Agreed,” Jackson added.

“Thanks,” said Jack.

Hiccup tried to blow Jack, but the position quickly became too much for his back. So he jerked him off instead. He was still pumping when Jackson warned them about the upcoming gas station and the boys had to fix their appearance.

After that, Hiccup drove and Jack and Jackson occupied the backseat. Jackson made sure Hiccup had a good view while he sucked Jack off. After a while the white-haired twin grabbed his brother’s head and started thrusting upward rapidly. Hiccup had a very hard time to stay focused on the road as Jack came vocally, fucking a load into his brother’s mouth. It was even harder when the twins switched roles and Jackson received a long, loving suck by his twin.

Drivings straight became downright impossible when Jack didn’t swallow all of Jacksons’ seed but instead made out with him. Two smoking hot twins, making out, sharing their load, showing tongue so now and again just to fuck with Hiccup.

They didn’t make it to their overnight target that day.

Instead, they just camped just off the Highway.

As promised, the Overlands put up the tent while Hiccup only had to set-up their little gas-burner to warm some canned foods. Jackson made a face at the beans he’d picked, while Hiccup contently nommed on his. He thought it was pretty good compared to his father’s ‘campsite cooking’. How that man managed to screw up even the easiest of canned foods was beyond Hiccup.

Jack was having some bread and spicy minced meat balls with chilly sauce. Jackson stole a bite and coughed.

“I added chilli paste”, his brother pointed out.

“And now you tell me?!” he wheezed. Jack just laughed.

“You better not give anyone a blow job anytime soon,” Hiccup warned. “I’m pretty sure that shit will burn down there too.”

“So no chilli paste as lube then?”

“Knock yourself out but leave me out of it,” Jackson laughed. His eyes were still teary from the spiciness.

 

*

 

The rest of the evening was spent talking about nothing in particular and gazing at the abundance of stars. When Hiccup decided he wanted to go to bed, both twins followed his example.

However, when they were all undressed and in their sleeping bags, it became clear they didn’t intend on letting him sleep soon. Jack gently cupped Hiccup’s face and kissed him. It was a tender, slow kiss, as loving as a kiss could get. When Jack broke away, Hiccup smiled.

“You really are dead set on making up for that stunt, aren’t you?”

“You bet we are,” Jackson said.

“Jackson can give one hell of a massage,” his brother pointed out. He gave another little kiss on Hiccup’s cheek. “You interested?”

“Isn’t that weird now we’re boyfriends?” Hiccup interjected.

His white-haired boyfriend shrugged. “I’m here too.” He kissed Hiccup again, this time deeply and with tongue, but just as loving. “Just lay on your stomach and enjoy.”

The brunet repositioned his slightly inflated member in his boxer briefs and lay down on his stomach as instructed. Jackson straddled him, putting his knees on both sides of Hiccup. His hands were soft and warm on Hiccup’s back.

“Just relax,” Jack whispered in his ear. He gently combed his fingers through the unruly, brown hair.

All tension quickly left him under Jackson’s deft hands. At some point there was the sound of a bottle opening and closing, and suddenly Jackson’s hands were slippery. It was cold at first, but it soon made the massage so much better. Hiccup melted into his air mattress, completely docile. The brunet twin slowly worked his way down Hiccup’s back, until he reached his ass. Hiccup expected him to stop there, but he went right on massaging, pulling down the red boxer briefs without hesitation. The brunet tensed but Jack kept whispering in his ear and playing with his hair as if nothing weird was going on. So Hiccup sighed and surrendered himself. Apparently this wasn’t his first time with Jackson anyway.

The brown-haired twin pulled the boxers all the way down and tossed them aside.

“Jezus,” he breathed.

“What?” Hiccup demanded, suddenly very insecure about himself. He was lying there stark naked after all.

“You’re so drop dead gorgeous.”

Hiccup blushed a deep, dark red.

“Jack, you lucky bastard,” Jackson continued. “Just look at that…” He rubbed his hands all along Hiccup’s back and down to his ass, giving it an appreciative squeeze. “… so hot.”

“Ehm… thanks?” Hiccup buried his burning face in his sleeping bag. He wasn’t exactly used to this. Sure, Jack told him he was beautiful. But not like this. Not with with the same mixture of horniness, hunger, and most of all admiration like Jackson did. He couldn’t mean every word more right now.

“He’s so right,” Jack mumbled in Hiccup’s ear, making him shiver. “You’re wonderful. I love you.”

Jackson moved down and started massaging the brunet’s legs, working his way up from his calves. Hiccup hated his legs. He hated how they were in some poorly defined state between hairy and smooth. But when he peeked at Jackson, the dork still wore the same look of admiration.

“All those beautiful freckles,” he whispered.

“Tell me about it,” Jack replied.

Jackson reached the brunet’s upper thighs. With each rub, his fingers got closer to the back of Hiccup’s sack, and it was driving him crazy. He was so hard right now. No doubt he was staining the sleeping back underneath him with precum. When the fingers finally touched him there, he moaned softly. It was but a fleeting touch, but he wanted so much _more_. God these boys knew how to turn him on.

“Sweet mother,” Jackson swore.

“So cute,” Jack agreed. To Hiccup, he whispered: “Don’t hold back. There is no-one but us around to hear.”

“I want to hear so much more,” said the other teen. He reached further, caressing more sensitive flesh. Hiccup sighed and lifted his ass a bit. The brown-haired twin chuckled and reached further, rubbing Hiccup’s entire package. Hiccup moaned.

Jack instructed him to turn over and left his side. The brunet obliged, revealing his rock-hard dick to the twins. Another curse from Jackson.

“When does the sexy end? This is just not fair.” Jack licked a nipple and received a jealous look from his brother. “And oh Lord he has a treasure trail.” He gently stroked it with his fingers till he bumped into the tip of Hiccup’s dick. The brunet wanted to hide forever, unable to process the lovely words, but he had nothing to hide behind.

Soon both twins were lying with their faces next to Hiccup’s crotch. Hands, mouth, and tongue were everywhere. They were rubbing his stomach and thighs. Touching his nipples. Gently massaging his balls.

Then there were lips on his balls. A testicle enveloped in the warm wetness of a mouth. Tongue dragging along his hard, leaking dick. Lapping at the precum at the head. Some suckling on his glans. A mouth bobbing up and down his shaft.

Every time they touched a new spot, Hiccup would curse or moan or gasp. The twins were delighted with the evident effect they had on Hiccup.

“He tastes so good too,” one of them said.

“And just the perfect size,” the other agreed.

“So smooth… We’re going to make you feel better than ever before, Hiccup,” Jackson promised him. Then he pushed a lubed finger up Hiccup’s ass. The brunet arched his back and gasped, but it was done gently, carefully. Jack moved up to face Hiccup, peppering him with kisses along the way. And while one brother prepared his ass for more, the other kept him distracted with loving words and kisses.

The concept of time was completely lost to Hiccup. All he knew where the sweet words and tender touches.

“Fuck me,” he said.

“Who?” asked Jack.

It was hard to think. “I don’t care. Either.”

Jack nodded and kissed him. He guided him onto his hands and knees, and Jackson lined up behind the gorgeous, freckled ass. The brown-haired twin pushed inside. He went slow, giving Hiccup time to get used to it.

“Ooooooh…” the brunet moaned. “Fuuuck you feel just like Jack.”

“You OK, Hic?” Jack asked. Hiccup looked up, seeing a worried look on his face. He must have looked as if in pain.

“I’m good. Go slow, but for Gods sake, start fucking me!”

The twin behind him laughed and slowly gyrated his hips, enticing more wanton sounds. Jack moved in front of Hiccup and offered him his dick. The brunet sloppily licked all over it. He loved giving blowjobs, but it was hard to focus in his current state of pleasure.

Jack groaned and pushed his crotch in Hiccup’s face, enjoying the warm wet of his tongue, while his brother slowly fucked the freckled boy between them. After a while, Hiccup tapped his boyfriend’s thigh. The white-haired teen moved back and Hiccup gasped for breath.

“Oh shit, sorry Hic.”

“It’s okay, I love your d-AAAAHHhhmmmn” Right then Jackson had pushed back in a lot faster than before. “Oh faaaack!”

“Sorry, too much?” Both boys were worried sick, but that was completely unnecessary.

“Fuck no, do that again!”

Relieved, Jackson pulled out and slammed in even harder. He got a similar response. He grinned at his brother and started to fuck the brunet in long, hard thrusts. Slowly out, fast back in.

Jack grinned back. The brunet’s mouth was hanging open. He considered offering his dick again, but Hiccup beat him to it. He pulled his boyfriend close and started to suck him off. It turned out to be quite hard to pleasure someone else while getting fucked so good. But Jack didn’t mind. This was all about Hiccup and no-one else. Besides, his mouth still felt great regardless of what Hiccup did. He gently moved his hips in sync with his brother, shallowly fucking Hiccup’s mouth. It was the right thing to do judging from the sounds the brunet produced.

Jackson picked up the pace. Pelvis and ass slapped together rapidly. He was breathing heavy. A few more thrusts, and he was at his limit. With a deep groan, he buried himself deep inside Hiccup, his balls pushing against the freckled ass cheeks. Hiccup moaned around Jack as he felt the member inside him pump and pulse. That was Jackson’s load in his ass. Not Jacks. Jacksons. It was one of the hottest realizations he’d ever had.

He moved his hips, grinding against the teen behind him throughout his orgasm.

When Jackson was done, he slid in and out a few more times, just to enjoy the feeling a bit longer. Then he pulled out.

Hiccup whined, but Jack was quick to move. He guided the brunet onto his back, putting his legs over his shoulders. Jack’s wet cock slid in effortlessly, and he picked up right where his brother had left off.

“Shit, sloppy seconds,” Jackson whispered. “So hot.”

Jack was too busy to reply. If he did this just right, Hiccup would-

“OOOOOH JACK!” Hiccup screamed. “Aaaaah yes like that! AH!”

Bingo.

Sloppy, slapping sounds filled the tent. Jackson watched breathlessly how his brother’s dick slid in and out. He realized he must have looked a lot like this a moment ago… and that was strangely sexy. A bit of cum was leaking from Hiccup’s ass, and he wiped it away with his fingers, touching Jack in the process. His brother groaned. Jackson touched him some more.

Hiccup managed a few words. “Uh aaah uh m-make me - oooh - cum!”

Jackson wrapped his hand around Hiccup’s leaking dick. He played with the foreskin and rubbed the head, jerking him off in sync with his brother’s thrusts. With just a few strokes, Hiccup exploded, sending cum all over his stomach.

During his orgasm, Hiccup clenched down, sending Jack over the edge too. His load was added to his brother’s.

Both rode out their orgasm. Then, Jack collapsed on top of Hiccup. He kissed his now boyfriend deeply.

“Did you like that?”

“Fuck yes,” Hiccup breathed.

“Are we forgiven now?”

“Hmmm…” the brunet pretended to think. “Not quite. I think I’ll keep you two on edge for a bit longer.”


	6. Day 6 - Double Penetration

**Summary for the Chapter:**

> A continuation of Day 5 - Hiccup is still on a roadtrip with the Overland twins. Jack has been a mischievous ass and needs to be punished...

**Notes for the Chapter:**

> A continuation of Day 5, although it is not neccessary to have read day 5 per say. I mean... It's not like there is some overarching story of any significance x"D Who has time for plot during HiJack Smut Week anyway?
> 
> Edit 24/9/2016: Added two lines I'd forgotten. Oops.

  
“Guys come on this is hardly necessary,” Jack pleaded

“Oh I beg to differ,” his brother said. “If we let you roam free you’ll probably flood the tent and set our shoes on fire or something. You’ve broken enough shit today.”

“You’re cursed,” Hiccup added. “And quite frankly also an idiot.”

Together they pulled Jack over to a nearby tree. Jackson held him – not that Jack was resisting that much – while Hiccup secured his hands to a tree with a length of rope.

“You have caused enough problems for today,” Hiccup said. “So while we roast marshmallows you’ll stay over here, safely out of the way.”

They were once again in the middle of pretty much no-where. Again, they hadn’t reached their overnight destination, this time through an unfortunate combination of backfired pranks and plain old bad luck on Jack’s side.

“It’s not like I was the cause of our flat tire!”

“No,” Jackson admitted, “but you were the reason I drove off the road in the first place. And that’s what caused the flat tire. So if you think about it, you kinda are to blame.”

“Not to mention the mess you caused on the back seat,” the brunet added.

“That bottle was just… broken!”

“You shook the soda on purpose, planning to give it to us. You were just too stupid to remember which ones were safe and which ones were ticking time bombs so you opened one yourself!”

“And then at that diner you added a shitload of tabasco hot-sauce to my food while I was taking a leak! My lips burned for over an hour!”

Jack laughed. “Oh come on that was hilarious! You should have seen your face!”

“Not funny,” Hiccup deadpanned. “The waitress thought he was dying.”

Jack smiled sheepishly. “Sorry… Look, it was just a rough day for all of us. Why don’t we just set up a little campfire, sit down, have a laugh, and go to bed?”

“Oh but we will,” Jackson said. “While you are tied up here.”

And with that, they turned their backs on the white-haired twin. Hiccup first helped Jackson with the tent. He then cleaned up the disaster Jack had left in the car while Jackson tried to get a fire going. It was already getting late, but they’d be damned if they didn’t at least roast some marshmallows before going to bed.

When Hiccup was done with the car, there still was no fire.

“Ehm… Jackson? What are you doing?”

“What does it look like I’m doing? The stupid wood won’t catch though.”

Jackson was doing his best to light a few logs… with a lighter. Just a lighter. The tiny flame was bravely licking at the big logs of wood - with little effect. Hiccup couldn’t hold it in and burst out laughing.

“You’ve got to be kidding me!” he howled. “Hahahahaha have you ever made a fire before? Oh sweet Jezus, thank you that I got to witness this!”

Jackson actually looked a bit hurt. “Well then you do it!”

“I’m sorry. I shouldn’t have trusted you city boys with this.” Still giggling, Hiccup showed him how to build a proper fire, using kindling and a newspaper to get it going. Within minutes they had some nice flames going.

“Guuuuys, can you untie me now? Come oooon!”

Hiccup threw a marshmallow in his general direction without even looking up. Both boys found a suitable stick and set to roasting fluffy, sugary goodness. It took some skill to get the perfect brown roast on the outside, and near-liquid awesomeness on the inside, but once you had it down, it was so worth it.

Naturally ‘city boy’ Jackson was less successful that marshmallow-veteran Hiccup. After one undercooked marshmallow, one lost to the flames, and another spontaneously combusting while still on the stick, Hiccup took pity on him. He offered him his own, nicely toasted marshmallow, earning Jackson’s everlasting gratitude.

The second donated marshmallow, they shared. Hiccup and Jackson exchanged a look. They were definitely on the same line right now. With a smile tugging at their lips, they moved closer together.

Closer.

Closer.

Their lips were almost touching. Hiccup opened his mouth…

“Jackson he’s miiiiine!” Jack yelled.

Touchdown. Jackson’s tongue slid past the brunet’s lips. They were kissing, right in front of Jack. And again, and again, and again. The sweet taste of marshmallow still lingered and Hiccup hummed in approval.

“Jezus Christ guys get a room! No wait don’t! Untie me first!”

Their tongues danced around each other, exploring. Jackson’s dick might have felt a lot like Jack’s, but his kissing was definitely different.

He felt Jackson’s hands on his ass, squeezing slightly.

“Hey Hiccup,” Jackson started, breaking away. “How about we fuck while Jack watches?”

“Can I do you?”

“Sure.” The brown-haired twin fetched the lube from their backpack and tossed it to Hiccup, who only barely caught it with fumbling fingers. Hand-eye coordination wasn’t one of his strong suits.

Jackson kissed him again. The brunet snuck a hand into the twin’s pants, groping his rapidly growing dick. Doing this with Jack - his fucking boyfriend - watching was already proving to be a huge turn-on.

And it would drive Jack insane. Win-win.

Hiccup dropped to his knees and undid Jackson’s pants, who simultaneously took off his shirt. The brunet pulled down the tight boxer briefs and a hard, cut cock bounced free.

“Hiccup noooooo don’t do this to me!”

“This is your punishment, Jack. Take it like a man.” He started to work on Jackson’s tasty member, slowly licking and sucking. He tried to figure out if he liked the same things as Jack, and he soon found there were some slight differences between the twins’ exact preferences. For instance, Jackson preferred to have his balls massaged harder than the soft, fleeting touches Jack loved so much. He also liked to be caressed in other places more, like his stomach or thighs. And most of all, he made more sounds.

The twin grunted and gasped and cursed under his breath. He whispered encouragement and praise, moaning softly when Hiccup did something particularly nice. The brunet was worried the guy would all too quickly unload in his mouth.

Thankfully, Jackson had enough stamina for Hiccup to give a thoroughly satisfying blowjob. Hiccup even got to jerk himself a little while doing it. By the time he stopped sucking, Jackson still hadn’t come yet and Jack was a blushing, whimpering mess by the tree.

Instead of preparing Jackson to be fucked, the brunet got a different idea.

“Have you guys ever gone all the way?”

Jack’s head shot up at that, distress in his eyes. Jackson blushed deeply and scratched his neck.

“Yeah… a few times, actually.”

“What do you guys normally do together?”

“This is awkward… Often we just jerk each other off and give oral. We’re only so good because we had plenty of practice. 69 is our all-time favourite position.”

Hiccup couldn’t help but imagine it. His dick twitched, jumping up and down at the thought.

“And if we’re in the mood, we fuck. We take turns who fucks who, because we both like giving and taking. But we have to be alone because I tend to get a bit loud… so it doesn’t happen that often.”

“Let’s fuck him together. At the same time.”

Both twins gaped at him.

“What?”

“Oh no no that will never fit!” Jack protested. “Better leave me tied up and alone then!”

“How exactly were you planning on doing that, Hic?” Jackson wondered.

“Well we have lots of lube, and I have an inflatable buttplug. We take our time, stretching him up nice and slow. And then we fuck him together.”

"Wait... you have an inflatable buttplug with you? On our roadtrip?"

"Shut up, Jackson. It's the HiJack Smut Week, don't question it."

Jack’s eyes went wide, but Jackson nodded. Before his brother could protest, he said: “Get the stuff.”

 

*

 

Jack whined against his brother’s lips as Hiccup squeezed the pump again, inflating the buttplug a bit more. He slowly moved it a bit, causing Jack to arch his back and groan.

Jack’s hands were still tied together, but he was no longer stuck to the tree. The other two made sure he didn’t touch himself though – that was a privilege only they were allowed. Jack was only going to cum when they wanted him to.

They had done a marvelous job keeping Jack distracted while they slowly stretched his ass further and further. Fingers touched, hands caressed, tongues licked and teased, and mouths pleased. Jack had never been this fucking horny before in his entire fucking life. And with a sex-loving brother like Jackson, that was quite something.

They had blown or jerked him to the edge of coming multiple times, only to stop again. Jack had whimpered an whined. His mind was a haze, overcome with pleasure.

“He’s ready,” Hiccup said.

Jackson lay down on his back and they guided Jack on top of him. Hiccup removed the buttplug.

“Nnnnmmm.” Jack bit down on his lip, squeezing his eyes shut. Jackson pulled him down and kissed him deeply while Hiccup lubed up his hardon. He twitched in anticipation of his brother’s ass.

He aligned his dick and pushed inside easily. Jack yelped. He’d never gone in this easily before though, that was definitely new. Jack really was stretched further than ever.

“Damn Hiccup, I think you actually did it.”

“Thanks. I actually do know what I’m doing, you know.”

“I shall never doubt you again.” Jackson thrust up a few times, effortlessly sliding in all the way. He then repositioned his feet for grip, and rapidly fucked his brother, who clung on to him for his dear life. His ass slapped against Jackson’s thighs; his dick was a blur. Jack moaned continuously. He’d never been fucked so hard before, and it was sooo good!

“Ooooooooh goooooood yes fuuuuck meeee!”

Jack’s dick was leaking, creating a little pool of precum on his brother’s stomach.

Jackson quickly got out of breath and slowed down again, much to Jack’s dismay. The white-haired teen was about to protest until he felt Hiccup’s fingers entering his ass as well. As Hiccup had hoped, the buttplug had done it’s job stretching. He moved in between Jackson’s legs and positioned himself. Slowly, he pushed inside.

The feeling was beyond divine.

His dick was squashed tight against Jackson’s, surrounded by Jack’s hot ass. It was still tight and Jack hissed in pain. Jackson started making out with him while Hiccup paused, giving him time to adjust.

After a while Jack started to wiggle his butt, his soft mewling going up a pitch from time to time when it felt particularly intense.

The brunet took that as a sign to push in for the rest of the way. His balls touched Jackson’s, and the tips of their dicks were pressed together hard.

“Oh my god,” Hiccup gasped in a hoarse voice. He could feel the edges of Jackson’s glans against his own. His foreskin had slid back, making it one of the hottest and most intense feelings he’d ever had.

Together, they started to move. It was awkward at first; finding a rhythm that worked with the two of them was difficult. But eventually they got it down, Hiccup doing most of the thrusting while Jackson got pleasure from both Jack’s ass and the dick that was rubbing along his own.

Jack was going crazy in between them. He cursed and groaned and begged for more.

Hiccup slapped his ass, getting a sweet little yelp.

“You like that? You like being fucked by your brother?”

“Oh god yeeeeeees hiccuuuup!”

“Does it feel good, two dicks inside of you?”

“Yes! Yes! nnnaaaaaaah!”

“Oh gods Jack it’s so tight,” Jackson added. “I feel Hiccup’s dick rubbing against my own. His dickhead rubs the underside of mine, it’s amazing!”

Hiccup thrust hard and Jackson groaned, his balls slapping against Hiccup’s harder than he was used to.

The brunet felt his orgasm approach. He thrust with abandon, holding on to Jack’s hips and fucking him roughly. The white-haired teen was almost screaming with pleasure.

Grunting, Hiccup came. Jackson could feel Hiccup’s dick pulse, and a new wetness spread around his own glans. He groaned at the hotness of it and tried to move more himself, desperate for his own release.

Hiccup wasn’t even done cumming when the other twin joined in, emptying his balls deep inside his brother.

Panting, they held still for a moment with a mewling Jack in between them. Hiccup’s dick slipped out, and Jackson felt a trail of sperm trickle down across his balls. He pulled out too and gently pushed his brother off. There was a sticky mess on their stomachs - Jack had come while they were pressed together, fucking.

They washed up with towels and water as best they could, both teens helping Jack. When they were done, Jackson carried him to their tent and they all settled in. Jack was in the middle, getting a hug from both Hiccup and Jackson at the same time.

“That was awesome,” he mumbled. Hiccup kissed his forehead.

“Good. Now try to get some sleep.”

“Though if I can’t walk tomorrow, you guys are totally carrying me everywhere.”


	7. Day 7 - Is this yours?!

**Summary for the Chapter:**

> Hiccup finds a very expensive piece of lingerie under the bed of his very gay, very hot roommate.

 

This was… unexpected. Hiccup just wanted to clean the room. He didn’t want to be confronted with this kind of information concerning his roommate. Yet here he was, holding a blue piece of silk trimmed with flowery lace. There was a fucking little ribbon on the front too. It was the first time he was even holding silk, and from the feel of it, this must be one hell of an expensive piece of underwear. Not to mention it was truly, undeniably sexy.

And he’d found it under Jack’s bed while vacuuming.

Honestly, he had not been looking for such personal items. In fact, he would have rather not known Jack had something like this in the first place. His roommate was already irresistible enough with his white hair and pale skin; Hiccup did not need to add one of the sexiest kinks of all time to his thoughts. It might just start another episode of misery and unrequited attraction all over again.

Before Hiccup could put it back and try to forget he’d ever seen it, his white-haired roommate walked in.

A greeting died on Jack’s lips when he saw what Hiccup was holding.

His first thought was ‘holy shit does Hiccup have one too?’ Then he realized how absurd that thought was, and that this was, in fact, his own piece of distinctly effeminate lingerie. His heart stopped. With eyes wide as saucers, a mouth dryer than the Sahara, and cheeks burning bright red, he stood nailed to the ground.

“Is this yours?” Hiccup asked, blushing equally vigorously.

“N-no,” Jack croaked. “It’s from a girl. Obviously.”

Hiccup arched his eyebrow in that stupidly attractive way of his. He did it while studying too.

“Jack, you’re gay. We both are.”

“Bi-curious adventure?”

“You described yourself as ‘gayer than Tom Cruise rollerblading in cut-offs’. Besides, no girl would leave underwear as expensive as this behind.”

Back at the start of the year, Hiccup had felt like he hit the jackpot. His roommate was funny, smoking hot in a goofy kind of way, _and_  gay! He’d been so happy when Jack came out to him right away, saying he didn’t want to hide anything now he was in college. That night had been liberating for both of them, laying the foundation for a strong friendship, and Hiccup often thought back on it fondly.

From time to time the brunet could swear there was a sexual tension between them so dense you could stick a knife in it. His roommate, however, never responded to the hints Hiccup kept dropping, so he eventually figured it was just him. He was probably sexually frustrated to such a level that he was simply imagining things.

Now Jack was in front of him, cheeks dark red, stammering like an idiot, and Hiccup wondered if he’d just been too subtle with his ‘hints’. Maybe there was something more.

“W-well I saw you dildo too!” Jack blurted out.

 _‘Oh shit oh shit abort fuckerdy fuck fuck!’_ was roughly Hiccup’s trail of thought.

“W-what? I-I don’t have a dildo!”

“Yes you do you keep it under your bed! Don’t think I don’t see you take things into the bathroom with you!”

“Still not a weird kink like ladies underwear!”

Jack’s chest tightened. Was that how Hiccup thought of this? A weird-as-fuck kink? So much for his hopes to ever become more than friends with the cute brunet…

Hiccup noticed the sudden sadness and realized he’d struck a nerve.

“Jack… I-”

“No, I get it. You didn’t need to see this.”

Oh sweet Odin Jack looked like a beaten puppy. He was even tearing up a little. It was like an arrow to the hart for Hiccup.

“I was lying!” He said. The other froze.

“What?”

“I panicked. Your kink i-isn’t weird at all!”

“You’re just saying that to make me feel better.” Jack took the delicate blue fabric from his hand.

“N-no I’m not! In fact I think it’s…” Hiccup took a deep breath. “It’s sexy. I think it’s hot when a guys wears this. No joke.”

Jack’s jaw hit the floor. Seriously? His cute roommate shared his fetish? Unbelievable. This must just be weird dream and he’d wake up any minute now.

“Can I ehm… you know…” Hiccup nervously fidgeted with the hem of his shirt. “Can I see you wear it?”

Jack pinched himself. He was very much awake. Eye contact was downright impossible at this point; both boys looked everywhere but at each other. Jack could feel his dick throb at the thought of wearing his favourite panties… especially with his roommate watching.

“You’d want that?” He croaked. He glanced at Hiccup’s crotch and saw a much more defined bulge than usual; it even twitched.

Hiccup nodded. “I-it’d be the hottest thing ever,” he admitted.

Jack gulped nervously and clutched the blue fabric in his fist. He didn’t trust his voice much, so after a simple ‘okay’, he disappeared into the bathroom to change.

 

*

 

Jack’s hand remained on the door-handle. His nerves were on fire and his stomach was filled with bees. Should he go through with this? Or maybe it was better to put his clothes back on and pretend this never happened. But then he might never get a chance to get together with Hiccup again, and that would be a dying shame, but on the other hand, he wasn’t sure if-

“Jack? Are you all right in there?”

That wasn’t a horny, impatient ‘where are you’. That was genuine concern. Hiccup was concerned about him. One simple question was enough to convey that Hiccup cared more about Jack than the sexy underwear, even in his undeniable state of arousal. Jack knew that, if he got dressed again and call the entire thing off, Hiccup would be fine with that too. They’d play CoD instead. And that gave him all the confidence he needed.

The door opened… and Hiccup was blown away. It was as if he saw Jack for the very first time. All pale, smooth skin in stark contrast with the dark blue panties; the patterns in the lace clearly visible, adoring his stomach and thighs with elegant flowers. But his posture was hunched, as if trying to hide. Hiccup tentatively took a step forward.

“You… you are so goddamn beautiful.”

Jack blushed furiously. “I feel overdressed though.”

“Sorry.” Hiccup threw his shirt aside in the blink of an eye. “Oh man I don’t know where to look. You’re…”

“Scrawny?”

“Fuck no. Drop dead gorgeous more like.” He let his eyes travel from the white shock of hair, down a positively kissable neck, over a simply perfect chest, and down a stomach he wanted to touch really badly. “Relax, man. If anyone could pull off that underwear, it’s you,” Hiccup assured him. “It. Is. Perfect.”

Jack relaxed a bit, showing more of himself. He moved his hands out of the way, giving Hiccup a perfect view of his taut crotch. The fabric was stretched tightly over his erection.

“Can I…”

“Touch me?”

“Kiss you.”

Jack nodded. His lips felt like sandpaper and his tongue was heavy. The bees in his stomach were in an uproar. But when Hiccup pressed their lips together, all that disappeared like snow in the sun. Those beautiful lips were soft and gentle, and the tongue against his was warm and wet and tasted a bit like chocolate.

The brunet wrapped Jack in his arms, the pale skin warm against his own. He ran his fingertips from the fluffy white hair down Jack’s back, all the way to the luxurious silk covering a wonderful, round butt. He let his hands run over the delicate fabric, squeezing the ass underneath it. Jack hummed into their kiss, quite content with the attention he was getting.

They broke apart for air, panting slightly. While moving apart, Hiccup pulled on Jack’s lower lip with his teeth, biting softly. Jack hissed.

“Please don’t do that.”

“Sorry.” Another soft, tender kiss instead. “Better?”

“Much better.”

“Bed?”

Jack nodded and they stumbled to Hiccup’s bed in a mess of kisses and giggles and soft touches. Jack tripped and fell down onto the bed with an indignant yelp, leading to more giggles. Hiccup discarded the rest of his clothes, carelessly tossing them aside. Jack barely got a chance to appreciate the sexy view of freckled skin and a hard dick pointing upward.

Hiccup lay down next to his roommate and kissed him deeply, slowly. Experimental, exploring touches. Mapping each other’s bodies. Which spots were sexiest, which gave the most pleasure, and which were just ticklish?

The brunet thrust his hips, moving against Jack’s hand on his dick. Meanwhile, he rubbed all along the length of his roommate’s member through the panties, enticing soft little moans. His fingers traced the contours of the sensitive flesh, rubbing just a bit harder at the edges of the glans.

“Any other kinks you want to act on?” He asked in a husky voice. “Or shall I suck you off?”

“Toys,” Jack breathed. “I want to try your toys.”

Hiccup smiled. He sat down on the ground and rummaged in the box under his bed a bit, looking for the perfect toy for Jack.

“Ah!” he found the vibo-egg. Now all he needed was his masturbator and- ah, there it was. He showed his picks to Jack for approval. The white-haired teen answered with a nervous smile and nodded.

“Do you want me to put it in?” Hiccup asked.

“Fuck yes.” Jack, still lying on his back, lifted his legs to his chest. He pulled the panties down a bit, fully exposing his wonderful ass to Hiccup. The brunet, still sitting on the floor at the edge of the bed, had a perfect view of his smoothly shaved, pucked asshole. Instead of just lubing him up, he moved his face closer. He gently squeezed Jack’s ass cheeks and moved them further apart. Jack yelped when he felt a warm, wet tongue instead of the cold lubed finger he’d expected.

“Oh fuck, Hiccup!” He cursed.

The brunet continued to lap at the spread ass in front of him, teasing the tight muscle with his tongue. So now and again he’d probe at Jack’s entrance, or move up and lick the back of his balls, dragging hot sighs and moans from his roommate. Jack was lost in pleasure; his mind was floating on a fluffy pink cloud in another dimension.

Hiccup used a bit of lube and fingered Jack briefly before pushing the egg inside. It was a small egg, so it didn’t need much preparation. He turned it on on the lowest setting and moved it around a bit inside Jack, until he found the right spot to push it against.

“OOOOoooohmmnn.”

Jup. That’s where the egg should be.

He got back on to the bed with Jack, who lowered his legs again and pulled the panties back up, once again covering his luscious ass. Hiccup lubed up the masturbator and slid it around his cock. It was a rather simple thing: a transparent silicone sleeve with ridges and nobs on the inside. But it felt good enough, and it was highly stretchable, which was crucial for what he was about to do.

The brunet pulled down the front of Jack’s blue-laced underwear, letting it bunch up below his balls. Hiccup was only a little bit jealous of how smooth this guy was… everywhere. It was no fair.

He lubed up Jack as well and wiped his hand on the sheets. Then he pulled the sleeve off his dick, straddled Jack, and pressed their slippery erections together.

“What are you doing?”

Jack immediately got his answer. Hiccup held their dicks snugly together and slid the sleeve on. Both boys groaned. It was tight. So tight, but at the same time so damn good. They could feel every ridge, every bump, rubbing along their lengths.

“Ooooh yesss…”

“Fuuuck, Jack,” Hiccup groaned. He held the sleeve still and started to fuck it. Their hard, leaking dicks ground together. He almost entirely pulled out and thrust back in till his glans popped out the top and their balls were pressed against each other. Everything was sticky. Wet. Soft.

Hiccup turned up the vibrations, setting the egg inside Jack’s ass to maximum.

“Shit!” gasped Jack. “I’m gonna cum!” His voice was the highest pitch Hiccup had ever heard him produce. He thrust harder, massaging the sleeve as well for maximum pleasure. With a loud groan, Jack came. Hiccup could feel the dick pulse and twitch against his own. He pulled the silicone sleeve back a bit further to expose the tip of Jack’s dick, and cum shot out across his stomach.

The brunet continued to pump when Jack was done, and the other teen writhed and groaned.

“Hiccup, stop! Aahhh! I’m too sensitive right now!”

Hiccup laughed and got off, gently pulling the silicone sleeve of their dicks. He saw some sperm was threatening to drip down onto the expensive lace, and he moved quickly to lick it away.

“Shit that’s hot,” Jack breathed. He pulled the brunet upwards to kiss him. They made out for a bit until the haze of Jack’s orgasm had cleared and he was fully back down on earth again. “Shall I suck you off?”

“Yes please.”

Jack pulled the egg out and got in position. Hiccup lay comfortably on his back, and Jack was sitting on hands and knees perpendicular to the brunet. Effectively, he was sucking him off from the side, granting his roommate a nice view of his body and blue-clad ass. Said roommate reached out and just managed to touch the soft butt while Jack worked on his dick.

He started out kissing and licking all over, lapping at the brunet’s balls while a small puff of pubes tickled his nose. But Hiccup was already hot and close to the edge - this was no time for a slow build-up.

“Please, just suck me,” he asked, an undertone of desperation in his voice. Jack giggled but obliged, taking as much of Hic’s dick as he could without gagging. He pumped his hand along his shaft in sync with the bobbing of his head. He went up and down, sucking hard and pleasing with his tongue, giving extra attention to the sensitive tip. As a cherry on the pie, he pulled up one of Hiccup’s legs, exposing his ass. With a wet finger, he probed a little, before pushing the still slippery egg inside.

The brunet gave a wanton moan. He squeezed down on Jack’s ass with one hand and burried the other in Jack’s white locks. His fervently sucking roommate pushed the egg deeper, and Hiccup came. He emptied his balls in Jack’s warm, hungry mouth.

Jack swallowed and came back up again. Hiccup was still basking in the afterglow, unable to produce more than incoherent sounds, completely at peace with the entire goddamn universe.

The white-haired teen snuggled up to him and kissed him. Hiccup opened his mouth and tasted himself, but he didn’t mind. On the contrary; it was rather hot. The taste of Jack combined with his own sperm… sperm that Jack had just swallowed most of. He was one lucky man.

“I’m gonna clean up…”

“So quick?”

“Do you know how hard it is to keep these clean? It’s silk!”

Hiccup laughed and watched Jack disappear into the bathroom and turn on the shower. Only then did he get up himself. He could have followed immediately, but then he would have missed the view of that beautiful ass.

 

*

 

Jack toweled his hair dry while Hiccup was cleaning the egg with toy-cleaner. He hugged his roommate from behind, kissing his neck. Hiccup instantly got goosebumps and he turned his head, trying to protect the ticklish spot. Jack was unfazed and just licked at his earlobe instead.

“Jaaack,” Hiccup laughed.

The white-haired man hugged his roommate tight, pressing his semi-hard dick against the bare freckled ass.

“Wanna go for another round?” He whispered. He could see Hiccup blush in the mirror.

“Do you, ehm…” The brunet hesitated.

“Yes?”

“Do you have something I could wear?”

Jack smiled. “I have a black thong. It would look great on you.”

“God yes,” Hiccup breathed.

“Do you want me to fuck you in it?”

“Maybe you should buy me dinner before we go that far.”

“I’ll buy you dinner tomorrow?”

“Deal.”

**Notes for the Chapter:**

> This one gave me so many ideas that I'll write an alternative version some time in the near future :x There was just too much that I wanted them to do and too little time to write it!


	8. Day 7.2 - Is this yours?! Bonus

**Summary for the Chapter:**

> An alternate version of Day 7 because I couldn't choose which one to go with. So I did both. Have fun.

**Notes for the Chapter:**

> "But J., you said you'd upload this within a week of smutweek?"  
> Hush, imaginary voice. Just enjoy the alternate version and no such difficult questions.

  
There was a tense silence between the two young men. Hiccup still had the dark purple fabric in his hand.

“Okay…” Jack started. “So maybe that’s mine.”

Hiccup couldn’t help himself and whispered ‘hot’, followed immediately by an inward curse. Him and his big mouth.

“What?”

“Nothing.”

“No no, not nothing. You just said ‘hot’ didn’t you?”

“Nope.”

“Yes you did.” Hiccup was a terrible liar at the best of times, let alone flustered and holding undeniably sexy lingerie.

“No, I didn’t. Honestly.”

“You’re into this too?”

“No. Yes. Fuck.”

“Wow,” Jack breathed. “Although fucking might be a bit abrupt though, you’d have to buy me dinner first.”

“F-” Hiccup caught himself making the same mistake twice. “Piss off.”

“So, do you you have any yourself,” Jack asked, getting back to the topic at hand.

“No… I never dared buy one. Thought it wouldn’t suit me.”

“Are you kidding me? You could rock that for sure!”

Another awkward silence, in which Hiccup’s only response was a dark blush at his roommates praise.

“Do you ehm… want to borrow them? They colour nicely with your dildo.”

“What?” The brunet’s eyes went wide. “How would you know?”

“I saw it lying around sometime, okay. I just had the grace not to say anything about it.”

“Oh. Well I was gonna put this back and pretend I hadn’t seen anything either, but you came in.”

“I just have bad timing?”

“That’s a matter of perspective. Cause now it’s out in the open… I could offer you the use of my toys in exchange? As long as you make sure to clean them properly after use.”

Now it was Jack’s turn to feel embarrassed again. He hadn’t dared to bring that up, but the idea had crossed his mind. Together with tons of lewd images with both him and Hiccup, but that was a different story entirely.

“I’ve ehm… always wanted to try something vibrating?”

Hiccup nodded thoughtfully and went over to his bed, pulling out his box of toys. He rummaged around in it with Jack looking over his shoulder, whispering an appreciative ‘damn’. This sexy fucker had about anything. In the brief moment Jack was looking, he saw handcuffs with a chain, a bright red dildo with a sizable knot, a vibrator, a smaller transparent dildo, a buttplug with a fluffy tail, and a bunch of cockrings. Why this guy had never bought lingerie was beyond Jack. It surely would compliment a collection like this.

Eventually, Hiccup got back up with a toy in each hand and a face redder than a fire truck.

“I have two you might like. Regular dildo with vibrator and a prostate vibo. I didn’t know what you were used to uhm… size-wise.”

“I’m used to nothing so I’ll take the smallest one,” Jack admitted. Hiccup handed him what he’d called the prostate vibrator. It was made of black silicone and it had a bit of an odd shape. “You just hold onto that pair I guess,” Jack said, referring to the lingerie his roommate still had.

“There is toy cleaner under the sink. I have condoms too if-”

“Thanks, but I’m good.”

Some more of that patented awkward silence. Neither really knew how to move on in this conversation, nor how to end it.

“Wanna try it now?” Hiccup blurted out.

“What?”Jack’s mouth fell open at the forwardness of his usually more private and held-back roommate.

“Sorrynevermindforgetisaidthat.”

“Wait-”

“I shouldn’t have said it. I didn’t mean to make you un-”

“That’d be fucking hot,” Jack interrupted him.

“Shit,” Hiccup cursed. His heart was beating in his throat. This was really gonna happen. Finally, he was going to see his drop-dead gorgeous roommate pleasuring himself. “I’ll take a quick shower. Be right back.”

Jack ended up taking a shower after Hiccup as well, and when he came back into their shared room, the brunet was lying on his bed in nothing but the purple, lace knickers. They fit him perfectly; the dark colour a stark contrast with his rather pale, freckled skin. Jack - who as already at half mast when he came out of the shower - went full-boner instantly. His roommate had his eyes closed. He was rubbing along the clear contour of his hard dick, obviously enjoying the sensation of the soft fabric.

“Fuuuuuuck,” the white-haired man swore, upon which Hiccup opened his eyes. He blushed furiously, but there was nowhere to hide.

Jack, not wanting to embarrass Hiccup by simply staring, dropped his towel and slipped on a different good-looking piece of lingerie. It was a black thong with a dark blue lace edge. His hardon didn’t fully fit underneath the small patch of fabric, so the tip was poking out the top. Jack loved how the edge rubbed just underneath his glans.

He made sure to bend over way more than necessary, giving Hiccup a good view of his ass. It would have been hilarious if it wasn’t so hot. He lay down on his bed and when he saw Hiccup staring, his dick jumped a little, a drop of precum leaking out the tip.

While Jack put a condom on the toy and lubed it up, Hiccup slipped his dick from it’s soft, fabric confines. His heart was beating in his throat. Jack was looking at him. Jack was staring at the body Hiccup himself had never found hot in any way, and yet there was obvious lust in Jack’s eyes. The intense stare by the white-haired man made Hiccup even hotter. He resisted the urge to fap furiously, determined to prolong this as much as he could. He looked at Jack, taking in every inch of his hot body, while he slowly stroked himself. The foreskin slid up and down smoothly, making soft slick noises. The pink, moist head was exposed on every downstroke.

Jack briefly halted his actions in favour of just jerking off while watching this smoking hot display across of him. He noticed Hiccup didn’t shave like himself, but rather trimmed things to acceptable levels. It was clean and practical, very much like Hiccup himself, and Jack decided it was hot as hell; he wanted to bury his nose in it while sucking off that glorious dick. Did he mention he had a thing for foreskin too? This auburn boy was his kink jackpot.

Balls showing at the edge of a thong on one bed versus a sack snugly covered in see-through lace on the other. Jack’s fist pumping slowly versus rapidly moving fingertips. Soft gasps and moans versus barely held-back groans of pleasure. Nervous smiles and brief, nervous eye contact.

Jack was going to cum too soon. In a feat of extraordinary self-control that probably originated in a desire to give Hiccup more of a show, he let go of his dick. Instead he fumbled with the toy, trying to get it in.

But Jack was nervous, new to the toy, and somehow not comfortable no matter how he was lying. He was starting to feel embarrassed, and that only made it worse, but he couldn’t give up either.

Luckily Hiccup took pity and came over.

“Do you need a hand?”

The gorgeous piece of hard meat was now much closer to Jack, and his eyes were fixed on the clear bulge. A damp spot was forming somewhere to the side, where the tip of Hiccup’s dick was situated. Jack swallowed hard.

“Do I look that awkward?”

“Yes. Get on your knees and move over.”

Jack did as he was told, getting on his hands and knees and making room for Hiccup to join him on the bed. The brunet got down behind him and took the already slippery toy. It almost shot from his hands, initiating some giggles.

He spread Jack’s soft, round ass-cheeks with his hands, admiring the feel of it. He pulled the thong aside with a thumb.

Jack held his breath in anticipation… and felt a much warmer, much wetter sensation than he’d expected. He moaned loudly as Hiccup licked his ass again. And again. And again. God this felt unlike anything he’d ever done before. He’d always found fingering a bit dull - it didn’t do that much for him and it wasn’t the most comfortable position. But this. Sweet motherfucking Jezus!

“OOoooooh fucking fuck Hiccuuuup,” Jack moaned. He almost whimpered when Hiccup’s tongue went in deeper. “You gotta let me do you this to you too, it’s sooo gooOOOOOHHHAaa! Fuck yes!” He carefully stroked the tip of his dick with his fingers, trying not to make too much friction lest he came right away.

“You’ll get your chance.” The brunet alternated the rimming with fingering, reveling in the sounds Jack would make. When his roommate was nice and wet, he replaced his fingers with the prostrate vibrator. He turned it up to max and gently pushed it in. When it settled into place, Jack groaned so loudly Hiccup pitied their neighbours in all directions. The white-haired man sunk down onto his stomach, lost in pleasure. Smiling, Hiccup lay back himself, rapidly jerking off. He watched as Jack bucked his hips, trying to fuck the bed for friction. He eyed the back of Jack’s smoothly shaved sack, and watched how the balls inside twitched every now and again. Every movement brought new sensations, leading to new sounds being emitted by Jack.

The brunet’s orgasm was fast approaching. Looking at Jack’s dick like that, he wanted a load in his mouth. That dick was out of reach though, so he lay on his back and rolled back as far as he could, putting his legs on either side of his head. With a few more strokes, warm seed dripped down into his waiting mouth.

Jack had rolled onto his back when he felt Hiccup move - which added yet another wave of sensation - and he’d seen the whole thing. Hiccup realized Jack was staring. He swallowed and blushed furiously, not knowing what to say.

The white-haired roommate was still in full-on horny bliss, however, and felt no embarrassment whatsoever. In fact, the line of cum below Hiccup’s chin looked incredibly lewd and a tad appealing. Jack got up - which caused the toy to hit him in yet another way - and moved over. Without hesitation, he licked the cum from Hiccup’s lip. The brunet opened his mouth in surprise and Jack took it as an invitation, kissing him deeply.

It didn’t last very long, however, since Jack was on the absolute edge himself.

“Can I…?” Jack gasped against Hiccup’s lips.

“What?” Hiccup had the feeling he knew what Jack wanted, but he wanted to hear him say it in that horny, husky voice of his.

“Fuck, Hiccup. Can I - hnmnn - cum in your mouth? Please?”

Hiccup grinned and nodded. Jack righted himself, offering his cut dick. The brunet sucked it in hungrily, humming in approval, and with only a few bobs of his head, Jack released a large load inside Hiccup’s mouth.

Jack moaned all throughout his orgasm, entangling his hands in his roommate’s hair. He pumped out several shots of cum while slowly moving in and out of Hiccup’s warm mouth. The brunet swallowed it all down. When Jack was finally done, he sat back, his wet member slipping from Hiccup’s mouth. There was a string of saliva connecting the dick to the soft lips and Jack’s heart skipped a beat. That was a sight he would never, ever forget.

Hiccup took a deep breath and wiped his mouth. Jack removed the toy and turned it off with a satisfied sigh. Suddenly completely drained, he flopped down on his back.

“Wow. That was intense.”

Hiccup crawled up and lay down half next to Jack, half on top of him. He kissed him, haring the taste of Jack’s come.

“You can say that again.”

 

* * *

 

 

When Jack stepped out of the shower for the second time that day, Hiccup was at the sink, cleaning the underwear. His precum had stained it.

The white-haired man stood behind him and wrapped his arms around the slightly smaller brunet. Hiccup giggled when Jack kissed his neck, and he could feel a half-hard dick pressed in between them.

“So. When do I get to do that to you?”

“Such a Casanova you. Didn’t you say something about buying dinner first?”

“We’ll get dinner tomorrow?”

“Deal.”


End file.
